How Do I Give Up Permanently?

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I can look back and say that I've never been popular with women. And it makes sense: I'm not very attractive, I'm introverted, not very dominant and I'm pretty pessimistic. If you're wondering, I have indeed asked a few out and it didn't work out too well. Except that I did date a girl for a few months when I was in college.

It was fun and she was very kind, but after a while I began sabotaging myself. After many years of just being bad at life, having someone be romantically interested in me didn't make any sense. And so I found some lame excuse to break up with her. And I can't really forgive myself for wasting her time like that. Not only that but she had this ability (or maybe I'm just an open book) to see things that I try to hide from other people, like my pessimistic attitude toward things. The vulnerability of it all really sucks, especially after the fact.

So I've been working on killing romantic feelings for anyone if they start to appear. It usually involves me not talking to them anymore. I know some older people who are divorced and alone and they seem like they're very comfortable with themselves and I would like to be like that.

It's just that occasionally when I'm alone, when I meet someone attractive or someone I get along with, this switch turns on that entertains the idea of dating someone and I can't make it stop.

Any Advice for this?

Before anyone entertains the idea that I shouldn't give up, let me make this clear - I don't have the mental ability to do it. I think that it requires a decent amount of self worth and mental stability and I just don't have it despite working really hard at it.

Help a guy find some resolve, please.